


Learning Something New

by FanRulerCass



Category: Undertale (Video Game)
Genre: Angst, Big Brother Sans (Undertale), Crossdressing, Fluff and Angst, Gender-Neutral Frisk (Undertale), How Do I Tag, Hurt/Comfort, Identity Issues, No Romance, but only society hurt him?, papyrus in a skirt
Language: English
Status: Completed
Published: 2018-12-13
Updated: 2018-12-13
Packaged: 2019-09-17 10:59:56
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,301
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16973349
Author URL: https://archiveofourown.org/users/FanRulerCass/pseuds/FanRulerCass
Summary: Frisk brought up a good point, why can't he wear that? No one is stopping him except himself. But that's all it takes.Basically Papyrus wants to wear a skirt and can't bring himself to.





	Learning Something New

**Author's Note:**

> Hope you guys like this! I have no beta so that's why this sucks but its a cute headcanon that I needed to release to the world. Enjoy!

Since moving to the surface Papyrus has found out about a handful of things. Humans are all very odd creatures. There are many, many different types of spaghetti. The shows that Alphys watched are not as realistic as they all thought. And most recently, people wear clothing that they feel represent them rather then the other way around.

While this is a common fact for many humans, those that were confined to the Underground were trapped back when people were stuck in their old ways. Times have changed and Papyrus is about to find out some things about him that he has never thought about before.

Currently, Papyrus was taking his favorite human shopping for some Gyftmas, or as the humans called it ‘Christmas’, gifts. They had a cart full of trinkets, games, and an obnoxious amount of pasta boxes.

While they were walking past the clothing racks to get to the check-out, Frisk ran over and grabbed a dress on display, putting it over their body and looking to Papyrus for approval. 

“WHY, THAT LOOKS LIKE IT IS JUST PERFECT FOR YOU!”

Frisk smiled widely, tossed the dress into the cart and signed, “I can wear it on our next date! Now I need to find something for you…”

They started looking around for something that Papyrus could possibly wear. With him being a rather big skeleton, and humans have not yet started producing monster-clothing quite yet, he mostly had to make due with whatever he could find.

He was admiring a particularly nice-looking box of noodles when a piece of clothing flew onto his head, followed by the sound of a child’s giggles.

“NOW, WHAT COULD YOU HAVE FOUND FOR ME, HMMM?” His boney hand removed the fabric and smoothed it out so he could see it.

It was a skirt. It seemed to be a longer one but would likely only reach right above his knee connections. A light blue color, with small frills along the bottom edge and small amount of sparkles within the frill to catch in the light. 

Papyrus…loved it. It was absolutely adorable. He looked down at Frisk who was trying to get his attention and signed, “That crop-top that you have would look really good with the skirt!” And they were right. He was envisioning himself wearing the combination and it made him feel…

“FRISK! WHILE WE BOTH KNOW THAT MY COOL SELF WOULD LOOK GOOD IN WHATEVER I WOULD WEAR, WE KNOW THAT I CAN’T WEAR…THIS.” He loosely shook the article, while shaking his head. He really hated to let the human down but it seems that no one ever taught them about these rules. That is why The Great Papyrus would be the one to help out!

“I WOULD NOT BE ABLE TO WEAR THIS SINCE I AM QUITE OBVIOUSLY A MALE!” He struck a ‘manly’ pose. “ONLY PEOPLE LIKE UNDYNE, ALPHYS, AND LADY ASGORE COULD!”

Frisk raised their arms to show they wanted to be picked up, which the skeleton quickly did. They situated themselves into the baby seat at the front of the cart, so they could be closer to equal high, making the conversation flow easier.

“If that is true, then am I ‘allowed’ to wear that?” They literally made quotation marks, mid-sign, and pointed to the dress in the cart. “Since I am neither what do I have to wear then?”

“WELL, UMM, YOU SEE…” Papyrus fumbled around for a response. He honestly didn’t have an answer. He really didn’t want to argue about this since he barely understood it himself, but were these not just universal rules? Like, this was just how the world was, right?

Frisk took advantage of this to cut in, “You don’t know, do you? People don’t think like that anymore. People can wear what they want and be who they are and like who they want. Do you think I’m bad for being me? Undyne and Alphys are bad for liking each other?”

His eyes flared a bright orange, agitated at the idea. “OF COURSE NOT! THAT IS JUST WHO YOU ARE AND THAT IS JUST WHO THEY…LIKE…” He trailed off realizing the flaws in his previous thoughts. Is it really okay? He has never been one to judge anyone for anything, so why is this such a big deal to him. 

“Its okay Papyrus, living where you all did trapped some ideas down there with you! Don’t feel bad, no one ever told you anything else. Do you want to still get it through?”

He shook himself out of his thoughts, that was an issue for another day. For now, he had to check-out and hope that he could find his car in the packed lot. He nodded his head and lifted the child out of the cart who ran ahead to get in line.

He ran a hand down the soft skirt which was still in his hand, thinking. He then bundled it up with Frisk’s dress at the bottom of the cart and went to get in line.

He didn’t see his friends smile at the gesture.

\---

It was late at night, late enough that Sans was likely to actually be asleep and Papyrus was still just lying in his bed.

All he could think about is the plastic bag containing a simple skirt tucked in the far corner of his closet. Under a blanket. In a chest. Just in case.

Even though it was over two days ago that he bought it, he still hadn’t tried it on or taken it out to even look at it again. 

He flipped over so he was staring at his closed closet doors and thought back to how he had gotten through the previous night.

After searching around online he finally figured out how to hide his search history. After that he spent hours browsing at different articles, blogs, websites, and pictures trying to understand.

The words: cross-dresser, drag, transgender, queer, genderfluid, masculine, feminine, and so many more passed over his mind, rolling on the edge of his metaphoric tongue. 

One posting he read last night would refuse to leave his head because it just felt so…familiar. 

It was someone telling their story about how much they loved this holiday called ‘Halloween’ where humans dress up for one night and go to parties, scary festivals, hunting for candy.

The reason they liked this holiday so much though was because they could dress up however, they wanted to and no one would judge them. While they were in a costume, gender did not matter because they could embody whoever they were pretending to be. 

Papyrus could understand this on a different level. He loved his Battle Body because then he would be intense and cool and not have to worry about his outfit for that day. He had always liked to dress up, even as a young baby bone.

Did this mean that he was one of those terms? He flopped around, facing away from the bed hoping to fall asleep and not be trapped with these thoughts anymore. That lasted all of ten seconds before he was sat in front of the open chest staring down at the plastic bag.

He gently took out the cloth and placed it on his lap, feeling the material. Suddenly, with bravery that seemed to come out of nowhere, he stood up, made sure his door was locked and the window blinds were closed, he stripped off his pajamas.

He slowly, delicately raised the skirt up to his hips and zipped up the back. He searched around his closet until he found the shirt Frisk mentioned and put that on as well. He took a deep, unnecessary breath before looking at himself in the full-body mirror on the closet door.

He looked very good. He felt very good. With the softest of touches he felt the fabric with his hands before smiling widely.

He jumped and took quick strides around the room, loving this new feeling of bare legs, with wisps of fabrics brushing the sides of him. He kept walking, faster and faster until he was almost running circles around his room.

He felt like a piece of him had just clicked in place. Until a knock startled him out of his daze and he tripped over himself and into the wall.

“hey bro? you doin okay in there? not that im complaining but youre making a lot of noise for so early in the morning.” It was Sans, of course it was Sans, who else could it be.

“UH BROTHER, GOOD MORNING! I AM MERELY UH TR-TRAINING! YES! THE EARLY SKELETON GETS THE EARLY…BIRD?” Papyrus cringed on the ground from his horrible lie. He just hopes his brother is too tired to dissect it much.

“you remember that the Guard was disbanded right? pap, you sure your okay? the past few days you have seemed off.” The door handle shook as he tried to open it. Papyrus mentally cheered since he thought ahead to lock it.

“YES, I AM FINE, THANK YOU VERY MUCH! AND I KNOW BUT I RATHER ENJOY THE EXERCISE! YOU MAY GO BACK TO BED I WILL SEE YOU LATER BROTHER!” Please go away, please go away, please go away.

“…okay whatever you say bro. get some sleep.” Light footsteps and a door click showed that he had gone back to bed. 

Papyrus kept laying on the ground for a solid five minutes before trying to quietly get up. His arms were shaking as he pushed himself into a sitting position. He suddenly felt oddly afraid.

It was merely his brother, he wouldn’t judge him, right? This was common, and nothing was wrong with him wearing these. Even with these hopeful thoughts, he almost shamefully took of the top and skirt and put them back into the bag in his closet.

Once he re-dressed, and laid back down in his bed he fell asleep with one thought.

Could Sans be ashamed of who I am if he found out?

\---

The following days resulted in a new founded awkwardness. Papyrus was insistent to explore this new world, but alone. It seemed so out in the open for others but as for him, he really did not know how to approach it.

He made several stops at multiple stores wearing various ‘disguises’ so he could remain anonymous. He failed to realize that he and his brother were the only skeletons in town, but thankfully for Papyrus no one commented.

He had spent many hours walking around different sections housing skirts while wearing a big hat and sunglasses. The few times assistances walked up to ask if he needed help, he freaked out and ran off leaving very confused humans in his stead.

While he still spent the same amount of time with his friends he would very quickly and obviously change the subject when any sort of clothing or honestly even society-type of topic would come up. 

When his friends would look at Sans in question for his brother’s odd behavior, even he would have a questioning look on his face. 

Nobody thought about asking Frisk if they knew what was going on.

\---

On the same night that the brothers had spent some time with their friends Sans decided it was time to get to the bottom of what was ailing his brother. He of course waited until after they were back home and Papyrus finished cleaning up the kitchen after their home-cooked dinner.

“hey paps i have a question for ya.” While he was choosing a movie for them to watch seemed like a perfect time to bring it up.

“I WOULD LIKE TO WATCH THAT ONE ABOUT THE CHILDREN WHO OWN THE HOTEL WITH DOGS! THAT ONE ALWAYS MAKES ME CRY!” With tears already in his eyes, he shouts over from putting the last dish away.

“heh while thats a real woofer, that wasnt what i was actually gonna ask.”

“THAT WAS ONE BAD AND YOU KNOW IT.”

“yea well making puns like these are no walk in the park.” Even though he can’t move his mouth, there is still a smirk on his face.

“UGH SANS! STOP! WHAT DO YOU EVEN WANT TO KNOW?”

Still chuckling, but slowing down to a more serious tone, “yea about that, its more that is there something you wanted to tell me? i mean this isnt the best way to put it but you have been…off the past while bro? is something going on?” 

By the time he was done with his sentence he already knew that he had hit the mark with how his brother seemed to retreat from the conversation. He had slowed his steps over to the couch and now just awkwardly stood next to it.

Sans had turned away from where had been kneeling on the ground looking for the movie. This seemed like something to really talk about and like hell would he let this pass over if it was bothering his little bro this much.

“THERE IS NOTHING TO WORRY ABOUT BROTHER! I HAVE JUST BEEN, UH THINKING MORE THAN NORMAL. JUST GETTING USED TO EVERYTHING UP HERE IS ALL! I WILL TRY TO FOCUS MORE, APOLOGIES FOR WORRYING YOU! I DO THINK I AM TOO TIRED FOR A MOVIE AT THIS POINT THOUGH, I WILL JUST BE IN MY…ROOM…”

“pap. what is going on. has someone been messing with you? cause they will have a bad time if so.” He had gotten up from his place on the ground and grabbed Papyrus’ wrist to stop him from leaving. His eye flared blue with his last declaration. 

“NO SANS NO ONE HAS DONE ANYTHING!” He jerked his wrist free, suddenly upset. “WHY DO YOU NOT BELIEVE ME? EVERYTHING IS PERFECTLY FINE, I AM PERFECTLY FINE. THERE HAS BEEN NOTHING NEW GOING ON AT ALL!” He was starting to get worked up at being pushed into this corner. He didn’t want to take it out on his brother, but he really wanted to get out of this conversation.

Thankfully Sans saw this and took a physical step back, but refused to back down. Paps had never hid anything from him before, so what is going on?

“i do believe you. but something is on your skull and i, i just want to be there for you. please let me know. im not gonna force ya but just let me help?” He hated not being able to help especially now that he knows for sure something is going on. He really didn’t want to push their trust but he would if that only meant that Papyrus would talk.

They both let silence wash over them. The taller of the two kept looking up towards his room and the ground at his feet. The shorter staring up at his brother hoping beyond hope he would say something.

“…”

“…”

“…I can show you…?” A timid and low voice broke the silence. 

“sure dude. where we goin?” Papyrus looked to his room again and made a motion to follow him up there. While Sans was confused why they would go to his room, he was just happy that some progress was being made.

Papyrus stopped outside his door and told Sans to wait outside while he quickly slid inside and closed the door behind him.

They both unknowingly leaned against either side of the door. One in relief and the other a bundle of metaphorical nerves.

He had no idea how he got himself into this situation. They were only supposed to watch a movie not confess his secret and much less show his secret! How is he going to react? He thought back to some stories that he read where people would go so far as disown each other. Sans wouldn’t do that…right?

Knock. “pap…not rushin you but are you ready to show me whats goin on?” He shakily shouted back to hold on and opened his closet. He must have been stood against the door longer then he thought. 

He slowly and quietly dressed in his skirt and shirt and walked to the door. He put his gloved hand on the doorknob, then leaned his fore skull on the door.

“Sans. I don’t know what you’re going to say.”

The door answered back, “im gonna say that I love ya still and we will get through whatever is goin on together. promise.”

The door opened. Silence resounded.

The small skeleton took advantage of the fact his brother had his eyes closed to examine what he saw before him. His brother was wearing a nice-looking shirt and a matching skirt. There didn’t seem to be any harm on him, only a tight look to his face.

“bro, im sorry, but i don’t get it. is someone making you wear this? is that the problem?” Had someone been blackmailing him into wearing these things or was something else amiss?

“No…I like wearing these. They make me feel – I feel good wearing these items brother! They just – just feel like they are meant for ME! AND I REALLY REALLY WANT TO KEEP WEARING THEM, EVEN OUT IN THE WORLD BUT I DON’T THINK YOU OR OUR FRIENDS WOULD LIKE THAT. I don’t – I don’t want you to be ashamed of me Sans.” 

“ashamed? paps what are you talking about? did someone say that to you? cuz nothing that you do could make me not wanna be with ya. youre my cool brother and nothing could change that dude.” Sans personally didn’t really understand the appeal of wearing them, both humans and monsters, but then again this is coming from someone who lived in his sweatpants and hoodie.

If Papyrus wanted to wear those then he damn well will wear them. And if anyone has any issue, they will have to answer to him. Because honestly, nothing his little brother could do could make Sans shamefully stand next to him. He will always be proud and acknowledge how he feels about his bro. 

“SANS, ARE YOU BEING HONEST? YOU’RE NOT DOING THAT THING THAT YOU SAY SOMETHING JUST TO MAKE ME HAPPY RIGHT? BECAUSE WE HAVE TALKED ABOUT THIS.” He was already feeling confident enough to raise his voice back to his normal speaking level.

Hopefully he was being honest. Maybe if Sans was okay with it, he could wear this more. He could even get more! There were so many to choose from. He could maybe even get some of their friends to help him choose his outfits, and then he could be the prettiest and coolest monster around. 

Wait, focus! 

“seriously bro, there is nothin wrong with you wearing any of that. is this what you were keeping from me? was this all?” Sans could see from the slightly dreamy look on his brothers face he was already zoning out into his dreamland which is a good sign.

“YES THAT – THIS WAS ALL BROTHER. I AM SORRY THAT I KEPT THIS FROM YOU BUT – “

“no, dont apologize. im sorry you felt you couldnt come to me about this to begin with. but hey, now we are all good, right? no more secrets?” He just needed one last confirmation before he could let this go.

Papyrus knelt down, sitting on his shins. He placed both hands on his older brothers’ shoulder and looked him straight in the eyes. 

Blue and orange flicked, facing each other.

“Nothing else.”

“nothing else.”

They dragged each other into a hug so tight they felt it in their souls.

They stayed like that for a long, long while.

\---

While Papyrus loved each and every gift that he was given for Gyftmas, the two new skirts he was gifted from his two favorite creatures he would treasure forever.


End file.
